U.S. Pat. No. 4,366,165 (Belgian Patent 867,245) discloses fungicides of the formula ##STR1## where Z is a C.sub.6 to C.sub.10 aryl radical;
R.sup.1 (in part) is CN, C.sub.1 to C.sub.12 alkyl or C.sub.3 to C.sub.8 cycloalkyl; PA1 R.sup.2 (in part) is H, C.sub.1 to C.sub.12 alkyl, or C.sub.3 to C.sub.8 cycloalkyl; PA1 m is 0 or 1; PA1 n is 0 or 2; and PA1 Q is a 1-(1,2,4-triazolyl) or 4-(1,2,4-triazolyl) radical. PA1 R (in part) is halogen, CN, NO.sub.2 or C.sub.1 to C.sub.4 alkyl; and PA1 R.sub.1 is one of OR.sub.2, SR.sub.2, N(R.sub.3)(R.sub.4). PA1 Ar is phenyl, pyridyl or thienyl each substituted with 1-3 substituents selected from R.sub.5, R.sub.6 and R.sub.7 ; PA1 Z is CH or N; PA1 Q is H, S(O).sub.n R.sup.18, halogen, CHO, C.sub.1 -C.sub.4 alkyl, or SH and its corresponding disulfide; PA1 n is 0, 1 or 2; PA1 G is ##STR4## where the nitrogen is bonded to the triazole or imidazole heterocycle; R.sup.1 is H, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 haloalkyl, (C.sub.3 to C.sub.6 cycloalkyl)methyl, C.sub.3 to C.sub.6 cycloalkyl, CH.sub.2 CO.sub.2 R.sup.10, (C.sub.2 to C.sub.4 alkenyl)methyl, (C.sub.2 to C.sub.4 haloalkenyl)methyl, CH.sub.2 SCH.sub.3, CH.sub.2 OCH, (C.sub.2 to C.sub.4 alkynyl)methyl, C(O)R.sup.12, C(O)(C.sub.1 to C.sub.4 haloalkyl), CHO, C(O)NH.sub.2, C(O)NHR.sup.12, phenyl or benzyl each optionally substituted with NO.sub.2, CN or 1 to 3 halogens; PA1 R.sup.2 is H, C.sub.2 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, cyclopropyl, CH.sub.2 CN, CO.sub.2 R.sup.11, CHO, CH.sub.2 OH, CN, C.sub.2 to C.sub.4 alkenyl or C.sub.2 to C.sub.4 alkynyl; PA1 R.sup.3 is pyridylmethyl, thienylmethyl, phenylmethyl, benzylmethyl, phenoxymethyl or thiophenoxymethyl each substituted with R.sup.8 and R.sup.9 on the aromatic radical and with R.sup.16 and R.sup.17 on the aliphatic carbon, phenyl substituted with R.sup.8 and R.sup.9, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.3 to C.sub.6 cycloalkyl, thienyl optionally substituted with 1 to 2 halogen, styryl substituted with R.sup.8 and R.sup.9, (C.sub.3 to C.sub.6 cycloalkyl)methyl, (C.sub.3 to C.sub.6 cycloalkyl)ethyl, pyrimidine or pyridine each substituted with R.sup.8 and R.sup.9 ; PA1 R.sup.4 is phenyl substituted with R.sup.8 and R.sup.9, benzyl substituted with R.sup.8 and R.sup.9, C.sub.3 to C.sub.6 cycloalkyl, thienyl optionally substituted with 1 to 2 halogen, styryl substituted with R.sup.8 and R.sup.9, pyridine or pyrimidine each substituted with R.sup.8 and R.sup.9, (C.sub.3 to C.sub.6 cycloalkyl)methyl, (C.sub.3 to C.sub.6 cycloalkyl)ethyl, OR.sup.13, SR.sup.13, or N(R.sup.14)(R.sup.15); PA1 R.sup.5 is H or halogen; PA1 R.sup.6 is H, halogen, methyl, CF.sub.3 or OCH.sub.3 ; PA1 R.sup.7 is H, halogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.1 to C.sub.2 alkoxy, CN, CO.sub.2 R.sup.12, NO.sub.2, S(O).sub.m CH.sub.3, phenyl optionally substituted with 1 to 3 halogens, or phenoxy optionally substituted with 1 to 3 halogen; PA1 m is 0, 1 or 2; PA1 R.sup.8 is H or halogen; PA1 R.sup.9 is H, halogen, methyl, CF.sub.3, OCH.sub.3, CN or CO.sub.2 R.sup.12 ; PA1 R.sup.10 is H, C.sub.1 to C.sub.6 alkyl, benzyl optionally substituted with 1 to 3 halogen, or phenyl optionally substituted with 1 to 3 halogen; PA1 R.sup.11 is H or C.sub.1 to C.sub.3 alkyl; PA1 R.sup.12 is C.sub.1 to C.sub.4 alkyl; PA1 R.sup.13 is C.sub.1 to C.sub.5 alkyl, (C.sub.2 to C.sub.4 alkenyl)methyl, (C.sub.2 to C.sub.4 alkynyl)methyl, phenyl substituted with R.sup.8 and R.sup.9, benzyl substituted with R.sup.8 and R.sup.9, C.sub.3 to C.sub.7 cycloalkyl, (C.sub.3 to C.sub.7 cycloalkyl)methyl or C.sub.1 to C.sub.5 haloalkyl PA1 R.sup.14 is H or R.sup.13 ; PA1 R.sup.15 is H, C.sub.1 to C.sub.4 alkyl, (C.sub.2 to C.sub.4 alkenyl)methyl or (C.sub.2 to C.sub.4 alkenyl)methyl; or PA1 R.sup.14 and R.sup.15 may together form a b 5-or 6-membered saturated heterocycle which contains the amine nitrogen and optionally a heteroatom of N, O or S; PA1 R.sup.16 is H halogen, CF.sub.3, OH, C.sub.3 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; PA1 R.sup.17 is H, F, Cl or CH.sub.3 ; PA1 R.sup.18 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CN, CH.sub.2 SCN; PA1 a) when R.sup.2 or R.sup.3 is CF.sub.3, then the other is not n-butyl; PA1 b) when R.sup.3 is phenoxymethyl or thiophenoxymethyl, then R.sub.16 and R.sub.17 are other than Br, I, Cl or OH. PA1 Q is H; PA1 R.sup.1 is H, C.sub.1 to C.sub.3 alkyl, allyl or propargyl; PA1 R.sup.2 is H, C.sub.1 to C.sub.3 alkyl, CN or C.sub.2 to C.sub.3 alkenyl; PA1 R.sup.3 is phenyl substituted with R.sup.8 and R.sup.9 ; phenylmethyl, pyridylmethyl, phenoxymethyl, thiophenoxymethyl, or thienylmethyl each substitut4ed with R.sup.8 and R.sup.9 on the aryl radical and R.sup.16 and R.sup.17 on the aliphatic carbon; PA1 R.sup.15 is C.sub.1 to C.sub.4 alkyl, (C.sub.2 to C.sub.4 alkenyl)methyl, or (C.sub.2 to C.sub.4 alkynyl)methyl; and PA1 R.sup.4 is phenyl substituted with R.sup.8 and R.sup.9, benzyl substituted with R.sup.8 and R.sup.9, C.sub.3 to C.sub.6 cycloalkyl, thienyl optionally substituted with 1 to 2 halogen, styryl substituted with R.sup.8 and R.sup.9, pyridine substituted with R.sup.8 and R.sup.9, (C.sub.3 to C.sub.6 cycloalkyl)methyl or (C.sub.3 to C.sub.6 cycloalkyl)ethyl; PA1 R.sup.5 is F, Cl, CH.sub.3 or CF.sub.3 ; PA1 R.sup.7 is halogen, CH.sub.3, OH.sub.3, CN, phenyl optionally substituted with 1 to 3 halogens or phenoxy optionally substituted with 1 to 3 halogens; PA1 R.sup.8 is H, F, Cl; PA1 R.sup.9 is H, F, or Cl.; PA1 R.sup.16 is H, F, Cl or C.sub.1 to C.sub.2 alkyl; and R.sup.17 is H. PA1 G is ##STR5## R.sup.1 is H or CH.sub.3 ; R.sup.2 is H or CH.sub.3 ; PA1 R.sup.3 is phenyl or phenylmethyl optionally substituted with 1 to 3 F or Cl and optionally substituted on alkyl with H or CH.sub.3 ; PA1 R.sup.7 is H, F, Cl, CH.sub.3, OCH.sub.3 or C.sub.6 H.sub.5 ; and PA1 Ar is phenyl, PA1 G is ##STR6## and R.sup.4 is phenyl substituted with R.sup.8 and R.sup.9.
European Patent 175,651, published Mar. 27, 1986 discloses microbiocides of the formula ##STR2## wherein A is phenyl, naphthyl, biphenyl, phenoxyphenyl or phenylthiophenyl;
L. Zirngibl, in Prog. Drug Res., 27 (1983), 253-383 reviews the field of antifungal monocyclic 1-substituted-1H-azoles.
None of the above suggests an imidazole or triazole linked from a nitrogen in the heterocycle to an external nitrogen atom.